Asymmetric induction using atropisomers: Diastereoselective additions to 2-acyl-1-naphthamides

Jonathan Clayden; Neil Westlund; Francis X. Wilson

doi:10.1016/0040-4039(96)01129-X

Asymmetric induction using atropisomers: Diastereoselective additions to 2-acyl-1-naphthamides

Jonathan Clayden^*, Neil Westlund, Francis X. Wilson

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

53 Citations (Scopus)

Abstract

The amide group of 2-acyl-N,N-dialkyl-1-naphthamides, twisted perpendicular to the naphthyl ring, controls the stereoselectivity of attack of nucleophiles on the 2-substituent. Selectivities of >140:1 may be achieved with bulky nucleophiles, which attack anti to the N,N-dialkyl group.

Original language	English
Pages (from-to)	5577-5580
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	31
DOIs	https://doi.org/10.1016/0040-4039(96)01129-X
Publication status	Published - 29 Jul 1996

Access to Document

10.1016/0040-4039(96)01129-X

Handle.net

Persistent link

Cite this

@article{56141a684421476aa9e62302d2532c80,

title = "Asymmetric induction using atropisomers: Diastereoselective additions to 2-acyl-1-naphthamides",

abstract = "The amide group of 2-acyl-N,N-dialkyl-1-naphthamides, twisted perpendicular to the naphthyl ring, controls the stereoselectivity of attack of nucleophiles on the 2-substituent. Selectivities of >140:1 may be achieved with bulky nucleophiles, which attack anti to the N,N-dialkyl group.",

author = "Jonathan Clayden and Neil Westlund and Wilson, {Francis X.}",

year = "1996",

month = jul,

day = "29",

doi = "10.1016/0040-4039(96)01129-X",

language = "English",

volume = "37",

pages = "5577--5580",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "31",

}

TY - JOUR

T1 - Asymmetric induction using atropisomers

T2 - Diastereoselective additions to 2-acyl-1-naphthamides

AU - Clayden, Jonathan

AU - Westlund, Neil

AU - Wilson, Francis X.

PY - 1996/7/29

Y1 - 1996/7/29

N2 - The amide group of 2-acyl-N,N-dialkyl-1-naphthamides, twisted perpendicular to the naphthyl ring, controls the stereoselectivity of attack of nucleophiles on the 2-substituent. Selectivities of >140:1 may be achieved with bulky nucleophiles, which attack anti to the N,N-dialkyl group.

AB - The amide group of 2-acyl-N,N-dialkyl-1-naphthamides, twisted perpendicular to the naphthyl ring, controls the stereoselectivity of attack of nucleophiles on the 2-substituent. Selectivities of >140:1 may be achieved with bulky nucleophiles, which attack anti to the N,N-dialkyl group.

UR - http://www.scopus.com/inward/record.url?scp=0030605902&partnerID=8YFLogxK

U2 - 10.1016/0040-4039(96)01129-X

DO - 10.1016/0040-4039(96)01129-X

M3 - Article (Academic Journal)

AN - SCOPUS:0030605902

SN - 0040-4039

VL - 37

SP - 5577

EP - 5580

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Asymmetric induction using atropisomers: Diastereoselective additions to 2-acyl-1-naphthamides

Abstract

Access to Document

Handle.net

Other files and links

Fingerprint

Cite this